Skip to main content
SpringerLink
Log in

Chemical and electrochemical preparation of poly(9,10-dihydrophenanthrene-2,7-diyl) using nickel complexes and electrochemical properties of the polymer

  • Published:
Polymer Bulletin Aims and scope Submit manuscript

Summary

Dehalogenation polycondensations of 2,7-dibromo-9,10-dihydrophenanthrene with isolated zero-valent nickel complex and electrochemically generated zero-valent nickel complex afford π-conjugated poly(9,10-dihydrophenanthrene-2,7-diyl). The electrochemically synthesized polymer is obtained as a thin film on electrode, and shows a reversible electrochemically doping-undoping cycle in an oxidation region. The polymer has essentially the same π-conjugation system as that of poly(p-phenylene).

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. T. A. Skotheim, ed., “Handbook of Conjugated Polymers” Vol. 1 and 2, Marcel Dekker, New York (1986)

    Google Scholar 

  2. H. Kuzmany, M. Mehring, and S. Roth. ed., “Electronic Properties of Conjugated Polymers”, Springer (1987)

  3. T. Yamamoto, Y. Hayashi, and A. Yamamoto, Bull. Chem. Soc. Jpn., 51, 2091 (1978)

    Google Scholar 

  4. N. Toshima, K. Tanaka, A. Koshirai, and H. Hirai, Bull. Chem. Soc. Jpn., 61, 2551 (1988)

    Google Scholar 

  5. E. Tsuchida, K. Yamamoto, T. Asada, and H. Nishide, Chem. Lett., 1541 (1978)

  6. P. Kovacic and A. Kyriakis, Tetrahedron Lett. 1962, 476

  7. T. Yamamoto, H. Wakayama, T. Fukuda, and T. Kanbara, J. Phys. Chem. in press.

  8. P. Kovacic, M. B. Feldman, J. P. Kovacic, and J. B. Lando, J. Appl. Polym. Sci. 12, 1735 (1968)

    Google Scholar 

  9. T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, T. Kanbara, S. Sasaki, and K. Kubota, Macromolecules, 25, 1214 (1992)

    Google Scholar 

  10. D. M. Ivory, G. G. Miller, J. M. Sowa, L. W. Schacklette, R. R. Chance, and R. H. Baughman, J. Chem. Phys. 71, 1506 (1979).

    Google Scholar 

  11. V. Percec, S. Okita, and R. Weiss, Macromolecules, 25, 1816 (1992).

    Google Scholar 

  12. T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, T. Kanbara, S. Sasaki, and K. Kubota, Macromolecules, 25, 1214 (1992)

    Google Scholar 

  13. T. Yamamoto, A. Morita, T. Maruyama, Z.-H. Zhou, T. Kanbara, and K. Sanechika, Polym. J., 22, 187 (1990)

    Google Scholar 

  14. T. Yamamoto, T. Ito, K. Sanechika, and M. Hishinuma, Synth. Met., 25, 103 (1988)

    Google Scholar 

  15. Chem. Ind. (London), 1988, 337

  16. T. Kanbara, N. Saito, T. Yamamoto, and K. Kubota, Macromolecules, 24, 5883 (1991)

    Google Scholar 

  17. M. Ueda, Y. Miyaji, T. Ito, Y. Oba, and T. Sone, Macromolecules, 24, 2694 (1991). These polymerization is based on organonickel C-C coupling reactions (e.g., T. Yamamoto, A. Yamamoto, and S. Ikeda, J. Am. Chem. Soc., 93, 3350 (1971); T. Yamamoto, S Wakabayashi, and K. Osakada, Organometallics, 428, 223 (1992); M. F. Semmelhack and L. S. Ryono, J. Am. Chem. Soc., 97, 3873 (1975)).

    Google Scholar 

  18. G. Bontempelli, F. Magno, B. Corain, and G. Schiavon, J. Electroanal. Chem, 103, 243 (1979)

    Google Scholar 

  19. G. Bontempelli, F. Magno, S. Daniele, and G. Schiavon, J. Electroanal. Chem., 159, 117 (1983).

    Google Scholar 

  20. J.-F. Fauvarque, M.-A. Petit, F. Pfluger, A. Jutand, C. Chevrot, and M. Troupel, Makromol. Chem., Rapid Commun., 4, 455 (1983)

    Google Scholar 

  21. G. Schiavon, G. Zotti, and G. Bontempelli, J. Electroanal. Chem., 161, 323 (1984)

    Google Scholar 

  22. G. Schiavon, G. Zotti, G. Bontempelli, and F. L. Coco, J. Electroanal. Chem., 242, 131 (1988).

    Google Scholar 

  23. D. E. Pearson, U. S. Patent 3988369 (1976)

  24. G. Wilke, Angew. Chem., 72, 581 (1960).

    Google Scholar 

  25. F. M. Jeager and J. A. van Dijk, Z. Anorg. Chem., 227, 273 (1936)

    Google Scholar 

  26. T. Yamamoto, A. Morita, Y. Miyazaki, T. Maruyama, H. Wakayama, T. Kanbara, S. Sasaki, and K. Kubota, Macromolecules, 25, 1214 (1992)

    Google Scholar 

  27. P. Kovacic, L. Hsu, J. Polym. Sci. Part A-1, 4, 5 (1966).

    Google Scholar 

  28. S. Sasaki, T. Yamamoto, T. Kanbara, A. Morita, and T. Yamamoto, J. Poly. Sci., Polym. Phys. Ed., 30, 293 (1992).

    Google Scholar 

  29. D. E. Stilwell and S.-M. Park, J. Electrochem. Soc., 136, 688 (1989)

    Google Scholar 

  30. B. Krische and M. Zagorska, Synth. Met., 28, C257 and C263 (1989)

    Google Scholar 

  31. H. Harada, T. Fuchigami, and T. Nonaka, J. Electroanal. Chem., 303, 139 (1991).

    Google Scholar 

  32. M. Sato and K. Kaeriyama, Makromol. Chem., 184, 2241 (1983).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Research Laboratory of Resources Utilization, Tokyo Institute of Technology, 4259 Nagatsuta, Midori-ku, 227, Yokohama, Japan

    Nobuo Saito, Takaki Kanbara & Takakazu Yamamoto

  2. Central Research Laboratory, General Sekiyu K.K., Ukishimacho, 210, Kawasaki, Japan

    Toshihiko Sato

Authors
  1. Nobuo Saito
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Takaki Kanbara
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Toshihiko Sato
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Takakazu Yamamoto
    View author publications

    You can also search for this author in PubMed Google Scholar

Rights and permissions

Reprints and permissions

About this article

Cite this article

Saito, N., Kanbara, T., Sato, T. et al. Chemical and electrochemical preparation of poly(9,10-dihydrophenanthrene-2,7-diyl) using nickel complexes and electrochemical properties of the polymer. Polymer Bulletin 30, 285–290 (1993). https://doi.org/10.1007/BF00343062

Download citation

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00343062

Keywords

Search

Navigation